Allyl bromide → HCID 86701780, Verbindung

HRID 2174134Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2174134
[C:1]([CH:3]([C:5]1[C:13]([O:14][CH3:15])=[CH:12][C:11]([CH3:16])=[C:10]2[C:6]=1[CH:7]=[CH:8][N:9]2[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH3:4])#[N:2].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH2:34](Br)[CH:35]=[CH2:36]>C1COCC1>[C:1]([C:3]([C:5]1[C:13]([O:14][CH3:15])=[CH:12][C:11]([CH3:16])=[C:10]2[C:6]=1[CH:7]=[CH:8][N:9]2[C:17]([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:18])([CH2:36][CH:35]=[CH2:34])[CH3:4])#[N:2]

Komponenten

5

Edukt 3

HCID 7841Allyl bromideHCID 2733832Lithium HexamethyldisilazideHCID 86701779HCID 86701779, Verbindung

Produkt 1

HCID 86701780HCID 86701780, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To (±)-tert-butyl 4-(1-cyanoethyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate (Example 156-A) (0.82 g, 2.61 mmol) in THF (13.04 ml) at −78° C. was added LiHMDS (1M in hexane, 3.13 ml, 3.13 mmol) and stirred for 7 minutes. At this point, allyl bromide (0.563 ml, 6.52 mmol) was added and the reaction stirred for 2 hours at −78° C. Reaction was then quenched with a saturated solution of aq. ammonium chloride and diluted with DCM. The layers were separated and the organic layer was dried over Na2SO4 and concentrated to an oil that was absorbed onto silica and purified via FCC (0-30% EtOAc:heptanes) to give the title compound. MS (ESI+) m/z 355.4 (M+H).

Aufarbeitung

  1. stirringthe reaction stirred for 2 hours at −78° C
  2. customReaction
  3. customwas then quenched with a saturated solution of aq. ammonium chloride
  4. additiondiluted with DCM
  5. customThe layers were separated
  6. dry with materialthe organic layer was dried over Na2SO4
  7. concentrationconcentrated to an oil that
  8. customwas absorbed onto silica
  9. custompurified via FCC (0-30% EtOAc:heptanes)

Quellen und Nachweise

ORD-Eintrag
ord-83a4eaed804a43c9820406c35ded5fa9
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09056874B2

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